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Tetrahydrofuran → 4-Chloro-6-(2-phenylethynyl)pyridin-2-amine

HRID 923664
Notes
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Reaction equation

HRID 923664 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[CH:11].C(N(CC)CC)C.C1COCC1>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C(#N)C>[Cl:8][C:6]1[CH:5]=[C:4]([C:11]#[C:10][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=[C:2]([NH2:1])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 53166492-Amino-4,6-dichloropyridine

Product 1

HCID 866943684-Chloro-6-(2-phenylethynyl)pyridin-2-amine

Reagents, catalysts & solvents 4

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418476HCID 178418476, compoundCatalyst
HCID 962WaterSolvent
HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

Dichlorobis(triphenylphosphine)palladium(II) (2.5 g, 3.06 mmol) is added to a mixture of 2-amino-4,6-dichloropyridine (5 g, 30.7 mmol), ethynylbenzene (7.05 g, 69 mmol), copper(I) iodide (0.58 g, 3.07 mmol), triethylamine (10.8 ml, 78 mmol), THF (25 ml) and ACN (50 ml) under argon atmosphere and is stirred at 90° C. for 17 h. The mixture is diluted with water (100 ml) and extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by NP chromatography. Yield: 3.52 g (50%). HPLC-MS: M+H=229; tR=1.85 min (METHOD—1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by NP chromatography

Sources & evidence

ORD record
ord-63ead371f50e48648c7e70d8155a9b9f
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278978B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes